1-[4-(2-Oxo-1,2-dihydropyridin-1-yl)phenyl]pyridin-2(1H)-one

The centrosymmetric title compound, C₁₆H₁₂N₂O₂, is composed of two pyridin-2(1H)-one rings linked to the para-positions of a central benzene ring via C—N bonds. Inter­molecular C—H...O inter­actions produce infinite mol­ecular sheets made up of R²₂(8) and R²₂(14) rings. C—H...π(arene) inter­actions inter­connect the sheets.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.111
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.797     0.991
            Tmin(prime) and Tmax expected:      0.966     0.991
            RR(prime) =      0.825
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and SADABS (Bruker, 2005); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXL97 and PLATON.

1-{4-[2-Oxopyridin-1(2H)-yl]phenyl}pyridin-2(1H)-one

Crystal data

C16H12N2O2	Z = 1
Mr = 264.28	F(000) = 138
Triclinic, P1	Dx = 1.444 Mg m^−3
Hall symbol: -P 1	Melting point = 591.3–592.9 K
a = 5.8911 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.7028 (13) Å	Cell parameters from 1306 reflections
c = 8.8707 (18) Å	θ = 2.5–30.6°
α = 76.50 (3)°	µ = 0.10 mm^−1
β = 71.33 (3)°	T = 295 K
γ = 67.44 (3)°	Plate, colourless
V = 303.99 (13) Å^3	0.35 × 0.19 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer	1396 independent reflections
Radiation source: fine-focus sealed tube	1064 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.797, Tmax = 0.991	k = −8→8
4208 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0464P)^2 + 0.076P] where P = (Fo^2 + 2Fc^2)/3
1396 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. R_F = 0.20 (CH₂Cl₂/MeOH = 95:5). ¹H-NMR (400 MHz, DMSO) δ 7.67 (d, J = 7.2 Hz, 2H), 7.53 (s, 4H), 7.51 (t, J = 7.2 Hz, 2H), 6.49 (d, J = 9.2 Hz, 2H), 6.32 (t, J = 6.8 Hz, 2H). ¹³C-NMR (100 MHz, DMSO) δ 161.8 (C=O), 141.4, 140.9, 139.5, 128.1, 121.3, 106.5.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6355 (2)	0.28659 (17)	0.69593 (14)	0.0490 (3)
N1	0.8798 (2)	0.39546 (18)	0.79369 (14)	0.0323 (3)
C1	0.7194 (3)	0.4297 (2)	0.69500 (17)	0.0346 (3)
C2	0.6677 (3)	0.6387 (2)	0.59727 (18)	0.0398 (4)
H2	0.5605	0.6727	0.5307	0.048*
C3	0.7703 (3)	0.7861 (2)	0.59958 (19)	0.0430 (4)
H3	0.7311	0.9198	0.5359	0.052*
C4	0.9366 (3)	0.7402 (2)	0.69739 (19)	0.0433 (4)
H4	1.0084	0.8417	0.6980	0.052*
C5	0.9889 (3)	0.5458 (2)	0.78984 (18)	0.0380 (4)
H5	1.1015	0.5125	0.8526	0.046*
C6	0.9406 (3)	0.1917 (2)	0.89808 (16)	0.0316 (3)
C7	1.1930 (3)	0.0645 (2)	0.88668 (17)	0.0358 (3)
H7	1.3218	0.1082	0.8109	0.043*
C8	0.7472 (3)	0.1287 (2)	1.01094 (17)	0.0357 (4)
H8	0.5783	0.2153	1.0182	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0586 (7)	0.0464 (6)	0.0562 (8)	−0.0299 (6)	−0.0295 (6)	0.0095 (5)
N1	0.0371 (6)	0.0287 (6)	0.0322 (6)	−0.0137 (5)	−0.0113 (5)	0.0019 (5)
C1	0.0337 (7)	0.0336 (7)	0.0366 (8)	−0.0122 (6)	−0.0110 (6)	−0.0003 (6)
C2	0.0397 (8)	0.0363 (8)	0.0394 (8)	−0.0093 (6)	−0.0151 (7)	0.0035 (6)
C3	0.0477 (9)	0.0287 (7)	0.0436 (9)	−0.0098 (6)	−0.0098 (7)	0.0039 (6)
C4	0.0538 (9)	0.0337 (8)	0.0455 (9)	−0.0221 (7)	−0.0101 (7)	−0.0018 (6)
C5	0.0445 (8)	0.0374 (8)	0.0370 (8)	−0.0192 (7)	−0.0120 (7)	−0.0023 (6)
C6	0.0369 (7)	0.0292 (7)	0.0306 (7)	−0.0138 (6)	−0.0121 (6)	0.0023 (5)
C7	0.0340 (7)	0.0375 (8)	0.0356 (8)	−0.0169 (6)	−0.0072 (6)	0.0019 (6)
C8	0.0312 (7)	0.0354 (7)	0.0377 (8)	−0.0105 (6)	−0.0094 (6)	0.0000 (6)

Geometric parameters (Å, º)

O1—C1	1.2334 (17)	C4—C5	1.349 (2)
N1—C1	1.4078 (18)	C4—H4	0.9300
N1—C5	1.3770 (17)	C5—H5	0.9300
N1—C6	1.4482 (17)	C6—C7	1.385 (2)
C1—C2	1.4430 (19)	C6—C8	1.386 (2)
C2—C3	1.348 (2)	C7—C8^i	1.3900 (19)
C2—H2	0.9300	C7—H7	0.9300
C3—C4	1.413 (2)	C8—H8	0.9300
C3—H3	0.9300
C5—N1—C1	122.18 (11)	C5—C4—H4	120.8
C5—N1—C6	118.79 (11)	C3—C4—H4	120.8
C1—N1—C6	118.98 (11)	C4—C5—N1	121.74 (13)
O1—C1—N1	120.32 (12)	C4—C5—H5	119.1
O1—C1—C2	125.01 (13)	N1—C5—H5	119.1
N1—C1—C2	114.67 (12)	C7—C6—C8	120.66 (12)
C3—C2—C1	121.94 (14)	C7—C6—N1	119.39 (12)
C3—C2—H2	119.0	C8—C6—N1	119.92 (12)
C1—C2—H2	119.0	C6—C7—C8^i	119.66 (13)
C2—C3—C4	120.95 (13)	C6—C7—H7	120.2
C2—C3—H3	119.5	C8^i—C7—H7	120.2
C4—C3—H3	119.5	C6—C8—H8	120.2
C5—C4—C3	118.42 (14)
C5—N1—C1—O1	176.33 (14)	C6—N1—C5—C4	−178.80 (14)
C6—N1—C1—O1	−1.1 (2)	C5—N1—C6—C7	−53.79 (18)
C5—N1—C1—C2	−3.4 (2)	C1—N1—C6—C7	123.74 (15)
C6—N1—C1—C2	179.18 (13)	C5—N1—C6—C8	124.49 (15)
O1—C1—C2—C3	−178.52 (16)	C1—N1—C6—C8	−57.98 (18)
N1—C1—C2—C3	1.2 (2)	C8—C6—C7—C8^i	0.3 (2)
C1—C2—C3—C4	0.8 (3)	N1—C6—C7—C8^i	178.53 (13)
C2—C3—C4—C5	−0.6 (2)	C7—C6—C8—C7^i	−0.3 (2)
C3—C4—C5—N1	−1.6 (2)	N1—C6—C8—C7^i	−178.52 (13)
C1—N1—C5—C4	3.8 (2)

Symmetry code: (i) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^ii	0.93	2.54	3.448 (2)	166
C7—H7···O1^iii	0.93	2.41	3.294 (2)	159
C8—H8···Cg1^iv	0.93	3.02	3.6814 (18)	129
C4—H4···Cg2^v	0.93	3.08	3.7015 (19)	125

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+2; (v) −x+2, −y+1, −z+2.